KR102080529B1 - Color filter comprising Green Dye and Display Device using the same - Google Patents

Abstract

(상기 화학식 1에서, 상기 R1 내지 R4는 각각 개별적으로 아릴기(aryl group)로 이루어짐)로 표현되는 화합물로 이루어진 것을 특징으로 하는 컬러 필터 및 그를 이용한 디스플레이 장치에 관한 것이다. The present invention comprises a green dye, the green dye is the following formula 1:
Formula 1

(In the formula 1, the R1 to R4 are each made of a compound represented by an aryl group (aryl group) respectively) relates to a color filter and a display device using the same.

Description

Color filter comprising Green Dye and Display Device using the same}

The present invention relates to a color filter used in a display device, and more particularly, to a green dye included in a color filter.

Display devices, such as liquid crystal display devices and organic light emitting display devices, have reduced the weight and volume, allowing the device to be enlarged, and also researching and developing in response speed and image quality. A lot of progress has been made in the current quality by continuing to progress.

Such a display device includes color filters of various colors to realize colors. Such a color filter includes a red (R) color filter, a green (G) color filter, and a blue (B) color filter. The green (G) color filter is a pigment-type material so far. Was mainly used.

The pigment-type material, which has been mainly used as a green (G) color filter, is shown in FIG. 1.

However, such conventional pigment type materials have limitations in reducing particle size because of poor solubility and dispersibility in solvents. Therefore, in the case of the conventional green (G) color filter, since the particle size is relatively large, there is a limit to improve light transmittance, a problem of light scattering occurs, and there is a problem of poor contrast ratio properties.

Japanese Patent Application Publication No. Hei 06-172361

The present invention was designed to solve the above-mentioned conventional problems, and the present invention is excellent in solubility and dispersibility in a solvent, thereby minimizing particle size, thereby improving light transmittance, reducing light scattering problems, and having excellent contrast ratio properties ( An object of the present invention is to provide a color filter comprising a dye-type material, that is, a green dye and a display device using the same.

In order to achieve the above object, the present invention comprises a green dye, the green dye is the following formula 1:

Formula 1

(In Formula 1, the R1 to R4 each provides a color filter characterized in that it is made of a compound represented by each aryl group (aryl group) individually.

The present invention also comprises a green dye, the green dye is the following formula 2:

Formula 2

(In the formula 2, the R1 to R4 each provides a color filter, characterized in that consisting of a compound represented by an aryl group (aryl group each individually).

The present invention also provides a display device comprising the color filter described above.

According to the present invention as described above has the following effects.

Particles constituting a color filter because the present invention uses a dye-type compound represented by Formula 1 or a dye-type compound represented by Formula 2, which is superior in solubility and dispersibility to a solvent, not a pigment-type material as in the prior art Since the size can be reduced, the light transmittance is improved, the problem of light scattering is reduced, and the contrast property is excellent as compared to the conventional one.

1 is a pigment-type material used as a conventional green (G) color filter.
Figure 2 shows the absorption spectrum of the compound represented by the formula (4) according to the present invention.
Figure 3 shows the absorption spectrum of the compound represented by the formula (5) according to the present invention.
4 is a schematic cross-sectional view of a liquid crystal display device according to an exemplary embodiment of the present invention.
5 is a schematic cross-sectional view of an organic light emitting diode display according to an exemplary embodiment of the present invention.

Hereinafter, preferred embodiments of the present invention will be described with reference to the drawings.

The color filter according to an embodiment of the present invention includes a green dye (Green Dye), and the green dye consists of a compound represented by the following Chemical Formula 1.

Formula 1

In Chemical Formula 1, each of R1 to R4 is individually composed of an aryl group. In Formula 1, the R1 to R4 may be made of aryl groups different from each other, but it may be advantageous in the manufacturing process that the aryl groups are identical to each other.

The color filter according to another embodiment of the present invention comprises a green dye (Green Dye), the green dye is made of a compound represented by the following formula (2). The compound represented by Chemical Formula 2 may be obtained through a ring contraction process for the compound represented by Chemical Formula 1 described above.

Formula 2

In Chemical Formula 2, each of R1 to R4 is individually composed of an aryl group. In Formula 2, the R1 to R4 may be made of aryl groups different from each other, but it may be advantageous in the manufacturing process that they are made of the same aryl group.

The compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 is not a pigment-like material as in the prior art, but is a dye-type material having excellent solubility and dispersibility in a solvent. Therefore, when the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 is applied to a green color filter, light transmittance is improved, light scattering problems are reduced, and contrast ratio characteristics are minimized by minimizing the particle size constituting the green color filter. It also becomes excellent.

In addition, the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 is useful as a color filter of a display device that must be manufactured at a low process temperature because it is possible to process at a relatively low temperature compared to a conventional pigmented material. Can be used.

On the other hand, in Formula 1 and Formula 2, the R1 to R4 may be composed of an aryl compound represented by the following Formula 3, respectively.

Formula 3

In Chemical Formula 3, R5 to R9 are each individually selected from the group consisting of hydrogen, C ₁ ~ C ₂₀ alkyl group, and C ₁ ~ C ₂₀ alkoxy group.

In particular, the green dye represented by Chemical Formula 1 includes a compound represented by Chemical Formula 4 below.

Formula 4

In addition, the green dye represented by Chemical Formula 2 includes a compound represented by Chemical Formula 5 below.

Formula 5

The compound represented by Chemical Formula 1 may be synthesized by preparing a phthalocyanine precursor and then cyclizing the prepared phthalocyanine precursor. In addition, the compound represented by Chemical Formula 2 may be synthesized by preparing a phthalocyanine precursor, performing a cyclization process on the prepared phthalocyanine precursor, and then performing a ring contraction process.

Hereinafter, a method for synthesizing a compound represented by Chemical Formula 5 as a representative of the compound represented by Chemical Formula 4 and a compound represented by Chemical Formula 4 as a representative of the Chemical Formula 1 will be described.

Scheme 1

As in Reaction Scheme 1 above, under nitrogen atmosphere, (a) compound 1,2-dicyano-3-nitrobenzene (5.0 mmol), (b) compound 2,6-di (Di ) -Tert-butyl (butyl) -4-methoxyphenol (1.5 equivalents), K ₂ CO ₃ (10 equivalents) was dissolved in 30 ml of anhydrous DMF and refluxed at 80 ° C. for 12 hours. (reflux) to react.

When the reaction is complete, the reaction solution is slowly dropped in ice-water. After that, it is extracted three times with methylene chloride (MC) and then passed through MgSO ₄ to evaporate and remove moisture.

Thereafter, the dried crude product is purified by column chromatography (MC = 100%) to obtain a compound (c), which is a phthalo nitrile precursor.

Scheme 2

As shown in Reaction Scheme 2, after dissolving (c) compound (2.38mmol) in xylene (50ml) and ethanol (10ml) under nitrogen atmosphere, Li (0.13g, 18.7mmol) was dissolved three times. Drop through the solution little by little.

Thereafter, the reaction was refluxed at 150 ° C for 5 hours. After that, the temperature of the reactant was lowered, followed by extraction with methylene chloride (MC) (100 ml) and washing several times with saturated brine. Thereafter, the remaining solvent is evaporated, and then purified by column chromatography with 100% of MC to obtain a compound represented by Chemical Formula 4.

Scheme 3

As in Reaction Scheme 3 above, the compound represented by Chemical Formula 4 (0.74 mmol) is dissolved in 30 ml pyridine, PBr ₃ (33.0 mmol) is added, and the temperature is raised to 120 ° C. and reacted for 2 hours. When the reaction mixture is distilled under reduced pressure (vacuum distillation) and the amount is reduced to 1 to 2 ml, the mixture is treated with CH ₂ Cl ₂ / MeOH (50/50) solution for 2 hours. The green solid after the reaction is dissolved in methylene chloride (MC) and filtered to remove excess pyridinium bromide. Thereafter, the filtrate is evaporated, dried in an oven, and purified by column chromatography (EA: HEX = 1: 7). After collecting the bright green band portion, it is dried under vacuum to obtain a compound represented by Chemical Formula 5.

Figure 2 shows the absorption spectrum of the compound represented by the formula (4) according to the present invention.

As can be seen in Figure 2, the compound represented by the formula (4) shows the maximum light absorption in the long wavelength band 641nm wavelength band, the maximum light transmittance in the medium wavelength band 509nm wavelength band, and the short wavelength band, the light absorption is improved. Can be. Therefore, it can be seen that the compound represented by Chemical Formula 4 can be usefully used as a material for a green color filter.

In addition, in the case of the compound represented by Chemical Formula 4, the light absorption rate in the long wavelength band and the short wavelength band decreases when the baking is performed compared to the case where baking is not performed, and as the temperature of baking increases, the long wavelength band and short wavelength increase. It can be seen that the light absorption rate in the band is further reduced. In particular, it can be seen that when the baking temperature is 230 ° C, the width of light absorption decreases in the long wavelength band and the short wavelength band is increased. Therefore, when the green color filter is formed using the compound represented by Chemical Formula 4, the baking temperature is 200. It may be desirable to make it below ℃.

Figure 3 shows the absorption spectrum of the compound represented by the formula (5) according to the present invention.

As can be seen in Figure 3, the compound represented by the formula (5) shows the maximum light absorption in the wavelength band of 670 ~ 680nm, the long wavelength band, the maximum light transmittance in the wavelength range of 550 ~ 570nm, the medium wavelength band, and the light absorption toward the short wavelength band It can be seen that this is enhanced. Therefore, it can be seen that the compound represented by Chemical Formula 5 can be usefully used as a material for a green color filter.

In addition, in the case of the compound represented by Chemical Formula 5, it can be seen that the light absorption rate in the long wavelength band and the short wavelength band is lower than that in the case where baking is performed when baking is not performed.

As described above, the color filter according to the present invention includes a green dye composed of a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 2, and further comprises a binder, an additive, and a solvent. Various materials known in the art may be used as the binder, additive, and solvent.

Hereinafter, various display devices using a green color filter including the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 will be described. The term "on" described below is meant to include not only the case where a certain component is formed on the right surface of another component, but also the case where a third component is interposed between these components.

4 is a schematic cross-sectional view of a liquid crystal display device according to an exemplary embodiment of the present invention.

As can be seen from FIG. 4, the liquid crystal display according to an exemplary embodiment of the present invention includes a first substrate 10 and a second substrate 20 facing each other, and the first substrate 10 and the second substrate 20 ) Is formed including a liquid crystal layer 30 formed on.

A thin film transistor T including a gate electrode 11, a semiconductor layer 13, a source electrode 14a, and a drain electrode 14b is formed on the first substrate 10.

Specifically, a gate electrode 11 is patterned on the first substrate 10, a gate insulating film 12 is formed on the gate electrode 11, and a semiconductor layer is formed on the gate insulating film 12. 13 is patterned, and the source electrode 14a and the drain electrode 14b are spaced apart from each other on the semiconductor layer 13. In the drawing, the gate electrode 11 is illustrated with respect to a bottom gate structure formed under the semiconductor layer 13, but the present invention is a top gate in which the gate electrode 11 is formed over the semiconductor layer 13 ( Top Gate) structure.

A protective film 15 is formed on the source electrode 14a and the drain electrode 14b. A contact hole is provided in the passivation layer 15, and the drain electrode 14b is exposed by the contact hole.

A pixel electrode 16 and a common electrode 17 are formed on the passivation layer 15. The pixel electrode 16 is connected to the drain electrode 14b through the contact hole. The common electrode 17 is arranged parallel to the pixel electrode 16, so that a horizontal electric field is formed between the pixel electrode 16 and the common electrode 17, and the liquid crystal layer ( The arrangement state of 30) is adjusted.

A light blocking layer 21, a color filter layer 22, and an overcoat layer 23 are formed on the second substrate 20.

The light blocking layer 21 serves to block leakage of light to areas other than the pixel area, and is formed in a matrix structure.

The color filter layer 22 is formed between the light blocking layers 21 of the matrix structure. The color filter layer 22 includes a red color filter patterned for each pixel, a green color filter, and a blue color filter. The green color filter constituting the color filter layer 22 includes a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 2 as described above.

The overcoat layer 23 is formed on the color filter layer 22 and serves to planarize the substrate.

The above is a liquid crystal display device of a so-called horizontal electric field method (In-Plane Switching mode) in which the arrangement state of the liquid crystal layer 30 is adjusted by a horizontal electric field between the pixel electrode 16 and the common electrode 17. Although described, the present invention is not necessarily limited thereto, and includes various liquid crystal driving methods known in the art, for example, twisted nematic (TN), vertical alignment (VA), or fringe field switching (FSF).

5 is a schematic cross-sectional view of an organic light emitting diode display according to an exemplary embodiment of the present invention.

As can be seen in FIG. 5, the organic light emitting diode display according to an exemplary embodiment of the present invention includes a thin film transistor T formed on the substrate 100 and an organic light emitting element E.

Specifically, a gate electrode 110 is patterned on the substrate 100, a gate insulating film 120 is formed on the gate electrode 110, and a semiconductor layer 130 is formed on the gate insulating film 120. ) Is formed in a pattern, and the source electrode 140a and the drain electrode 140b are spaced apart from each other on the semiconductor layer 130. In the drawing, although the gate electrode 110 is illustrated with respect to a bottom gate structure formed under the semiconductor layer 130, the present invention is a top gate (where the gate electrode 110 is formed over the semiconductor layer 130). Top Gate) structure.

A protective layer 150 is formed on the source electrode 140a and the drain electrode 140b.

A color filter layer 160 is formed on the passivation layer 150. The color filter layer 160 includes a red color filter, a green color filter, and a blue color filter patterned for each pixel. The green color filter constituting the color filter layer 160 includes a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 2 as described above.

A planarization layer 170 is formed on the color filter layer 160. A contact hole is provided in the passivation layer 150 and the planarization layer 170, and the drain electrode 140b is exposed by the contact hole.

A first electrode 180 is formed on the planarization layer 170. The first electrode 180 is connected to the drain electrode 140b through the contact hole. The first electrode 180 may function as an anode.

A bank layer 190 is formed on the first electrode 180. The bank layer 190 is formed in a matrix structure to define a pixel area.

The emission layer 200 is formed in the pixel region defined by the bank layer 190. The emission layer 200 is formed on the first electrode 180. The light emitting layer 200 includes a host material that emits a predetermined light and an organic layer made of a dopant material, and in addition, a hole injecting layer and a hole transporting layer , Electron injection layer (Electron injecting layer), and an electron transport layer (Electron transporting layer).

A second electrode 210 is formed on the emission layer 200. The second electrode 210 may be configured in the form of a common electrode, and thus may be formed on the entire surface of the substrate including the bank layer 190. The second electrode 210 may function as a cathode.

The above has described the organic light emitting display device according to one form to which the color filter layer 160 is applied, but the present invention is not limited thereto, and various types of top emission (Top) known in the art to which the color filter layer is applied emission) and bottom emission type organic light emitting display devices.

10: first substrate 20: second substrate
30: liquid crystal layer 22, 160: color filter layer
100: substrate 180: first electrode
200: light emitting layer 210: second electrode

Claims (9)

delete delete delete delete It comprises a green dye, the green dye is the formula 2:
Formula 2

(In the formula (2), R1 to R4 are each individually composed of an aryl group (aryl group))
Color filter characterized in that it is made of a compound represented by. The method of claim 5,
The R1 to R4 are color filters, characterized in that made of the same aryl group. The method of claim 5,
R1 to R4 are each of the following Chemical Formula 3:
Formula 3

(In the formula (3), R5 to R9 are each independently selected from the group consisting of hydrogen, C ₁ ~ C ₂₀ alkyl group, and C ₁ ~ C ₂₀ alkoxy group)
Color filter, characterized in that consisting of an aryl compound represented by. The method of claim 5,
The green dye is the following Chemical Formula 5:

Color filter characterized in that it is made of a compound represented by. A display device comprising the color filter according to any one of claims 5 to 8.

Images